Transitioning from practicing law to owning and operating a scalable business requires a fundamental mindset shift - one that many attorneys struggle to make. When Rochelle Oldfield founded Oldfield Law in September 2019 after two decades as a prosecutor, she quickly realized that winning cases for the government hadn't prepared her to run a private practice, manage finances, or lead a team.
In this raw and transparent episode for the Beyond the Bottleneck series, Rochelle opens up about early operational stumbling blocks, including "working for free" due to arbitrary flat-fee pricing and carrying an unsustainable 75-case load on her own. She walks through her firm's ultimate trial by fire: experiencing mass staff turnover while attending a Law Firm Mentor retreat, leaving her with a brand-new associate and a severe financial mess to fix.
Rather than giving up, Rochelle took immediate, decisive action. Through strategic coaching, she overhauled her billable models, embraced financial transparency with her staff, and rebuilt her team from one person to eight dedicated team members. Today, Oldfield Law has grown its average monthly revenue from $48,000 to $80,000, putting the firm on track to hit $1.2 million - all while allowing Rochelle to step into her role as CEO and reclaim her personal time without guilt.
What You'll Learn- From Prosecutor to Founder: How 20 years in child welfare and government prosecution prepared - and didn't prepare - Rochelle to run a business.
- Overcoming Mass Turnover: How Rochelle navigated losing her entire staff at once and rebuilt a higher-caliber team.
- The Danger of Arbitrary Flat Fees: Why guessing flat-fee costs leads to working for free and how to transition to proper billable models.
- Financial Transparency as Leadership: How sharing firm revenue and overhead numbers with staff creates accountability and healthy competition.
- Shifting from Lawyer to CEO: Overcoming imposter syndrome to build a mission-driven firm that serves community needs.
- Reclaiming Personal Freedom: How building proper operational support allowed Rochelle to reduce her caseload from 75 to 25 and eliminate founder guilt.
Helpful Links- Law Firm Mentor Website
- Deb Bilbao on LinkedIn
- Rochelle Oldfield on LinkedIn
- Oldfield Law Official Website
Episode Highlights- 00:00:00 – Rochelle Oldfield’s Journey from Prosecutor to Law Firm Owner
- 00:11:44 – Stop Guessing on Pricing and Start Data-Driven Billing
- 00:20:52 – Reframe Your Identity: You're a CEO First, Attorney Second
- 00:24:04 – Unite Your Team Around a Clear, Community-Focused Vision
- 00:28:51 – Share Financial Reality to Build Accountability and Ownership
- 00:31:32 – Delegate Real Authority and Watch Your Team Step Into Ownership
- 00:39:17 – Commit to Bold Action Over Perfect Analysis - Your Setbacks Are Steps, Not Failures
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Notable Guests IncludeRochelle Oldfield, Abigail Seymour, Bridgette Bennett, Jennifer Emmaneel, Roxanne Jen, Danielle Hendon, Ted DeBettencourt, Pam Meissner, Steve Fretzin, and other industry experts in legal marketing, leadership, and law firm growth.
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